Phenoxyethyl-dimethyl-dodecyl-ammonium halides



Patented Jan. 8, 1 952 PHENOXYETHYL-DIMETHYLZDODECYL- AMMONIUM m rrors" Max 'Hartmann and Werner Bosshard, Riehen, Switzerland, assignors to Ciba Pharmaceutical Products, Inc., Summit,-N.--J.

No'Drawln'g." Application December 19, 1949, se rial No. 133,952. In Switzerland November 24,

2 Claims. (01. zoo- 567.6)

This application is a continuation-impart of our copending application Serial No. 622,690, filed October 16, 1945, now abandoned.

It is known that aryloxyalkyl-ammonium compounds which are derived from bivalent phenols have disinfectant properties. These compounds are not entirely satisfactory from; the standpoint of activity and, moreover, entail the disadvantage that the starting materials required more prep- This is realized by the present inventionjac cording to which disinfecting and-*preservin'g' preparations are obtained by the production or a phenox-yethyl dimethyl dodecyl ammonium 1 halide of the formula on; *om

HF- ommcHi- 1 wherein Hal stands for achlorine or a bromine atom. An advantage of a the present' inventionthus resides in the use of starting materials of simpler-constitution; the products-thus obtained having surprisingly more valuable properties than theabove named compounds. V

In addition to their characteristic of having a dodecyl group linked to the quaternary jmtrog'efi" atom, it is further prerequisite to 'theachievement of the results sought by the present inven tion that the activecompounds'be dimethylated at such nitrogen atom and that the benzene nucleus of the-phenoxymoity'thereof be'f-reeof substi'tue'nts. These conditions are: satisfied byeach- 0f these compounds.

To produce the new compounds, phenoxyethyll ethyl-dimethylamine named asrstar-ting material dimethyl-amine is quaternatedawith. .dodecyl chloride or wdodecyl bromide.-- =-The=. phenoxy--' is known'.-- It may be prepared, for example, by I reacting phenoxyethylene with methylamine and subsequently methylating the obtained fl-phenoxyethyl-methyl-amine with formic acid and formaldehyde'i The new compounds may furthermore be produced also by causing phenoxyethyl-chloride or bromide to act on dimethyldodecylamine.

The products resulting from the instant process are soluble in water and constitute well crystallizing compounds. Their disinfecting and preserving properties are good and they are suitable'as'-'disinfectant and preservative preparations for a very wide range of application. They may be used for disinfecting the skin, for in-' stance the hands, instruments, bandage material, washes and the like, as well as for disinfecting or preserving human or animal foodstufis. They may be used'aloneor mixed in theform of solutions or emulsions and/or in admixture with other active or inert substances, such as salves, or as dusting powder.

As hereinbefore indicated, it has been found that, in order to realize the desideratum of the present invention, it is essential that the benzene nucleus of the phenoxy moiety'of the active compounds according to the invention, be free of substituents and, more especially, free of substituents containing three or more carbon atoms. It is also essential that thealkyl groups attached to the quaternary nitrogen" "comprise two "methyl groups andone dodecyl group. I The following table shows a comparison of disinfectant activity between, on the one hand,a preferredand represent'ative compoundaccording to the invention, 1

and on the other hand relatedcompounds where in, however: I

(a) The benzene nucleus of the 'phenoxy moiety is substituted; v I

(b) The N-lower alkyl' substituents on the quaternary nitrogen are other than methyl ro ps; and" (c) There is no aliphatic hydroc'arbon radical,

on the said nitrogen atom -with 12 carbon atoms.

4 3 Table Bacteria coll Substance 932: Min- CH: CH: 1 -0CHr-CH N(CH1M.CH: moon 2 CH: CH: 1! Hi H n O-GHr-CH: -o mooo 234- CH: CH: OCnHa In o-om-om- Ncnr wow so i cm on. IV @o-em-cmMcnQ mooo 2% uHn CH; CH: v o-onrcn, on, n-om mono 60 a CH: CH3

VI O-0Ha-CH,N-(CH -GH: mono 60 on; em vn @o-ore-cnr -Nc11,- 1:1000 60 51 CH: CH:

VIII (t)-H;1Cr-O-CHzCHg-E(CH2)n-Cfh 121000 2% The procedure followed in obtaining the foregoing results is as follows:

The antiseptic is tested in series of 4 concentrations in peptone bouillon tubes. 0.2 cc. of a 24 hour old microbe culture is introduced into each of the four tubes at intervals of 30 seconds. The tubes, when ready for the experiment, contain an average of 5 cc. After 2 minutes of contact, a loopful of the contents of each tube is transferred by means of a platinum loop into 5 cc. of fresh bouillon. These transfers are renewed every 2 /2,minutes, i. e. at the end of 5, 7 /2, 10, 12 15 minutes, etc.

The simultaneous testing of a series of 4 concentrations of antiseptic is the maximum which still permits of careful manipulations and transfers. The subcultures containing the transferred material are put into an incubator where they are left for 4 days at 37 C. A control tube without antispetic substance permits of the verification of the regular growth of the germs in question.

The table indicates the dilutions in which the compounds concerned have a bactericidal effect after a specified period of time.

The following example illustrates the invention but is not to be regarded as limiting it in any way, the parts being by weight:

Example 7 parts of p-phenoxyethyl-dimethylamine are Z5 heated for 2 hours on the boiling water-bath with 11 parts of dodecyl bromide. A good yield of 18- phenoxy ethyl dimethyl dodecyl ammonium bromide is obtained which, after recrystallization from acetone, melts at 112 C. It is a white crystalline powder which dissolves easily in water to give a neutral reaction.

If, in the same manner, dodecyl chloride is reacted and th heating time is extended to 20 hours or if the bromide obtained as described above is shaken with silver chloride in alcohol for 20 hours at room temperature, p-phenoxyethyl- .dimethyl dodecyl ammonium chloride is ob 2,581,336 5 6 1. A fi-phenoxylethyldimethyl-dodecyl-am- REFERENCES CITED momum halide of the formula The following references are of record in the E file of this patent: @WOEOHHHIM 5 UNITED STATES PATENTS Number Name Date wherein Hal stands for a member of the group 2,471,622 Hartmann et a1. May 31, 1948 consisting of chlorine and bromine atoms.

2. 3 Phenoxyethyl dimethyl dodecyl am- FVOREIGN PATENTS monium bromide of the formula 10 Number Country Date a CH3 CH3 484,906 Great Britain May 9, 1938 493,865 Great Britain Oct. 17, 1938 72,039 Norway May 5, 1947 z-(CHzhoCEI: MAX HARTMANN. l5

WERNER BOSSHARD. 

1. A B-PHENOXYLETHYL-DIMETHYL-DODECYL-AMMONIUM HALIDE OF THE FORMULA 